Acetyl chloride → HCID 11490985, compound

HRID 2114168Notes

Reaction equation

HRID 2114168 reaction equation
[CH2:1]([O:3][C:4](=[O:48])[C:5]([CH2:17][O:18][C:19](=[O:47])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]2[C:31]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=3)=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:29])=[C:23]([OH:46])[CH:22]=1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(N(CC)CC)C.[C:56](Cl)(=[O:58])[CH3:57]>C1(C)C=CC=CC=1>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:17][O:18][C:19](=[O:47])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]2[C:31]([C:36]3[CH:37]=[CH:38][C:39]([C:42]([F:44])([F:43])[F:45])=[CH:40][CH:41]=3)=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:29])=[C:23]([O:46][C:56](=[O:58])[CH3:57])[CH:22]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:48])[CH3:10]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 23641307HCID 23641307, compound

Product 1

HCID 11490985HCID 11490985, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

2-(2-{3-Hydroxy-4-[(4′-trifluoromethyl-biphenyl-2-carbonyl)amino]phenyl}acetoxymethyl)-2-phenylmalonic acid diethyl ester (0.200 g) obtained in Example 1-a) was dissolved in toluene (4 mL), and to this solution was added triethylamine (0.040 g). After dropwise addition of a solution of acetyl chloride (0.026 g) in toluene (1 mL), the resultant mixture was stirred at room temperature for 1 hour. The reaction solution was diluted with toluene (5 mL) and washed with saturated aqueous sodium bicarbonate (5 mL), 1N hydrochloric acid (5 mL) and water (5 mL). The toluene layer was concentrated and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=2:3) to give the title compound (0.165 g) as a colorless crystal. The physicochemical properties of the product are shown in Table 3 below.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (5 mL), 1N hydrochloric acid (5 mL) and water (5 mL)
  2. concentrationThe toluene layer was concentrated
  3. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=2:3)

Sources & evidence

ORD record
ord-5015f64d803045c1b3cef44158bc7b54
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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